The Outline, Joshua Topolsky’s newest venture, wants to run unusual long-form content. For example, a recent article that drew raves even from KellyAnne Conway, was titled “Diet Coke Is Not Killing You,” and another was called “Why Do We All Have Balls on Our Hats.” Today, you can read the explainer “What is Hygge.” You get the idea.

Topolsky is a well-respected tech editor, having first been editor-in-chief of Engadget, and after that a co-founder of The Verge. He left there for a stint at Bloomberg, from which he was unceremoniously fired by Michael Bloomberg himself. After a while, he was able to raise $5 million to launch The Outline. It wasn’t easy, as we in the industry know about the business model problems for digital publishers.

Topolsky proposes to fund The Outline through advertising, but a better form of advertising. He’s been quoted as saying he plans to run “better ads.” In the issues I’ve read so far, the major advertiser, who really is more of a sponsor, has been Cadillac. Cadillac ads appear in two formats: as snippets of Cadillac-related history and statistics between stories, and mi-story as a trilogy of cards that draw attention by moving from askew to in a row. The cards are odd, but you do see them, and at least one other earlyadvertiser, Method, is trying them. As for the Cadillac-related “branded content,” or “native advertising,” or whatever you’d like to call it, that occurs between stories in a large block, easy to mistake for another story.

There is no question these ads are visible. And I suspect there’s no question consumers recognize — at least after a while — that they’re advertising. But in the industry, there’s quite an uproar about how openly branded content is labeled, and although the mid-story ads are labeled “advertisement,” that label is in very small type and in light gray. Easy to miss. Not only that, but there’s no way to close out a piece of native advertising; you just have to scroll past it.

From the advertiser’s perspective, it’s perhaps more troubling that the landing page has no ads at all, and ads only appear when you click on the Read More. The site is very design heavy, and the stories are presented in an infinite scroll. Cadillac has clearly paid the most for its sponsorship, because it’s content is baked into the design of the site.

Obviously the jury’s out on whether this will work. On a recent Recode Media podcast, Jessica Lessin said it’s pretty easy to get the initial four advertisers to commit to trying a new digital media site. The trick is whether any publisher, including Topolsky, can get them to come back repeatedly. If Cadillac were to continually commit, and the traffic grows on the site beyond the initial readers curious about what Topolsky is doing next, perhaps they and he can build an effective brand partnership.

That, however, would depend on how much Cadillac knows about its customers and Topolsky knows about his traffic.